CN108658804A - The preparation and application of the supermolecular gel factor and its organogel of the one kind based on three columns [5] aromatic hydrocarbons - Google Patents
The preparation and application of the supermolecular gel factor and its organogel of the one kind based on three columns [5] aromatic hydrocarbons Download PDFInfo
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- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
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- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
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- G01N21/64—Fluorescence; Phosphorescence
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Abstract
It is a kind of organogel factor based on column aromatic hydrocarbons of complexity of column [5] aromatic hydrocarbons and the synthesis of pyromellitic trimethylsilyl chloride nucleo philic substitution reaction modified by amide the invention discloses a kind of supermolecular gel factor being based on three columns [5] aromatic hydrocarbons.The gelator can form the organogel of the aggregated-state induced fluorescence with blue by C H π, π pi accumulations and Van der Waals force in cyclohexanol.In organic machine gel, it is separately added into Hg2+, Ca2+, Mg2+, Ni2+, Cr3+, Cd2+, Pb2+, Ag+, Zn2+, Ba2+, La3+, Eu3+, Tb3+Aqueous solution, only Hg2+Addition the blue-fluorescence of organogel can be made to quench, and additions of other cations have no apparent influence to the fluorescence intensity of organogel, therefore it being capable of single-minded selective fluoroscopic examination Hg2+, and detection is limited to 1.02 × 10‑8M。
Description
Technical field
The present invention relates to a kind of supermolecular gel factor based on three columns [5] aromatic hydrocarbons and its synthesis；The present invention also relates to simultaneously
And organogel based on the gelator and also identify Hg in fluorescence2+Application, belong to compound synthesis field and sun from
Sub- detection technique field.
Background technology
Column aromatic hydrocarbons is a kind of ring being formed by connecting in the contraposition of phenyl ring by methylene by hydroquinone or Hydroquinone ether
Shape oligomer.From Ogoshi in 2008 it is that this macrocycle molecule with special property is named so far, column aromatic hydrocarbons is after from first
Step synthesizes, structure is explored, and to processes such as further functionalization, the exploration of Subjective and Objective complexation property, self assembly researchs, development is swift and violent,
Its status in supermolecule host-guest chemistry is increasingly prominent.Since with various excellent performances, column aromatic hydrocarbons is increasingly becoming this
The research emphasis in field.Although the supramolecular organogel based on column [5] aromatic hydrocarbons has been reported, it is based on three columns [5]
The supramolecular organogel of aromatic hydrocarbons and the stimuli responsive property that it has widely are studied not yet.
Invention content
The first object of the present invention is to provide the supermolecular gel factor and its synthesis side of the one kind based on three columns [5] aromatic hydrocarbons
Method；
The second object of the present invention is to provide the organogel based on the above-mentioned supermolecular gel factor；
Third object of the present invention is to provide above-mentioned organogels in fluorescence identifying Hg2+Application
One, the supermolecular gel factor
It is column [5] aromatic hydrocarbons modified by amide and equal benzene front three the present invention is based on the supermolecular gel factor of three columns [5] aromatic hydrocarbons
A kind of organogel factor based on column aromatic hydrocarbons of complexity of acyl chlorides nucleo philic substitution reaction synthesis, molecular formula are
C146H153N6O36, it is named asC 3 Type column [5] aromatic hydrocarbons is labeled as JP5.
The synthesis of supermolecular gel factor JP5：Make solvent, amidated column [5] aromatic hydrocarbons and equal benzene front three with dichloromethane
Acyl chlorides is with 1:3 molar ratio, in 10 ~ 12h of room temperature reaction；It waits for filtering after reaction, obtained solid is washed with dichloromethane, very
Sky is dry, and product is gelator JP5.
The synthesis of amidation column [5] aromatic hydrocarbons sees reference document：Q. Lin, X. M. Jiang, L. Liu, J. F.
Chen, Y. M. Zhang, H. Yao, T. B. Wei, Soft Matter, 2017,13, 7222-7226。
Two, supramolecular organogel
Above-mentioned supermolecular gel factor JP5 is dissolved by heating in cyclohexanol（The mass volume ratio of gelator JP5 and cyclohexanol
For 50 ~ 60mg/mL）, it is cooled to room temperature, forms the stable supramolecular organogel with the aggregated-state induced fluorescence of blue, mark
It is denoted as JP5G.It is 58 ~ 60 DEG C that organogel JP5G, which turns solubility temperature,.
The hexamethylene alcoholic solution of JP5 is in λexThere is no fluorescence when=345nm, as JP5 is converted to gel, gel state by solution
Under JP5G there is the strong aggregated-state induced fluorescence of blue（As shown in Figure 1）.
Three, test experiences of the JP5G to cation
1, JP5G is to Hg2+Fluorescence response
Dose volume is 500 μ L in gel bottle（Gel strength is 50mg/mL）Supramolecular organogel JP5G, use capillary
Choose a fritter gel to be placed on spot plate, the aqueous solution of different cations is added in the gel on spot plate respectively（C=
1mol/L, Hg2+, Ca2+, Mg2+, Ni2+, Cr3+, Cd2+, Pb2+, Ag+, Zn2+, Ba2+, La3+, Eu3+, Tb3+）, liquid level is made not have just
Gel is crossed, and is placed on the variation for observing its fluorescence color under the fluorescent lamp that wavelength is 365nm.As a result, it has been found that only as addition Hg2+
When the blue-fluorescence of JP5G can be made to quench, and addition of remaining cation influences the fluorescence intensity of JP5G without apparent, says
Bright JP5G being capable of single-minded selective fluoroscopic examination Hg in aqueous solution2+。
2, JP5G is to Hg2+Titration experiments
It is 200 μ L that a volume is prepared in particle fluorescence colorimetric pool（Gel strength is 50mg/mL）Supramolecular organogel
The Hg of different equivalents is added into JP5G by JP5G2+Aqueous solution（C=0.1mol/L）, with fluorescent spectrophotometer assay, the gel is glimmering
The variation of luminous intensity.With Hg2+Be gradually added into, the fluorescence intensity at 486nm gradually weakens JP5G to Hg2+Fluoroscopic examination
It is limited to 1.02 × 10-8M（As shown in Figure 2,3）, illustrate JP5G to Hg2+Detection it is sensitiveer.
3, interference--free experiments
It is 200 μ L that 13 parts of volumes are prepared in particle fluorescence colorimetric pool（Gel strength is 50mg/mL）Supramolecular organogel
The ion of 1 times of equivalent is added in JP5G in gel（Hg2+, Ca2+, Mg2+, Ni2+, Cr3+, Cd2+, Pb2+, Ag+, Zn2+, Ba2+, La3 +, Eu3+, Tb3+, volume is 39 a concentration of 0.1mol/L of μ L）, its fluorescence intensity is measured, is then added respectively in above-mentioned ionic gel
Enter 1 times of equivalent（Volume is that 39 μ L ion concentrations are 0.1mol/l）Hg2+, measure its fluorescence intensity（As shown in Figure 4）.From figure
We can see that the presence of other cations is to Hg2+Fluorescence identification JP5G be no any interference, illustrate its have compared with
Good interference free performance.
Three, JP5 self assemblies identify Hg2+Mechanism
1, JP5 is self-assembly of the mechanism of organogel
The compound JP5 for weighing different quality concentration respectively makes its nuclear magnetic spectrogram, as shown in figure 5, the quality of gelator according to
It is secondary to be（a）0.005g；（b）0.01g；（c）0.015g；（d）0.02g；（e）0.025g；Volume V=0.6ml.We can from Fig. 5
To find out, with the increase of JP5 concentration, the Hydrogen Proton H on the aromatic ring of centergIt is moved to High-Field, the Hydrogen Proton H on column aromatic hydrocarbons aromatic ringc
It is moved to low field, in addition to this Hydrogen Proton He, Hf, Ha, HbIt is moved to low field, this is because with the increase of concentration, JP5 molecules
Between by C-H π, the interactions such as π pi accumulations and hydrogen bond carry out self assembly, and the hydrogen on its corresponding position is caused to occur
Movement forms the organogel with condensed state.
2, JP5G identifies Hg2+Mechanism
Hg is identified in order to verify JP5G2+Mechanism, we have made JP5 powder, and Hg is added in JP5G xerogel and JP5G2+It is dry
The infrared and scanning electron microscope of gel.From Fig. 6 it will be seen that the stretching vibration peak difference of the-N-H and-C of JP5G xerogel=O
In 3300 and 1676cm-1Locate appearance, but as addition Hg2+After, the stretching vibration peak of-N-H and-C=O move to 3420 Hes respectively
1651cm-1Place, illustrates that intermolecular hydrogen bond is destroyed.We are from scanning electron microscope（Fig. 7）It is also seen that corresponding variation, JP5
The club shaped structure of rule is presented in the structure of powder, and after self assembly occurs for JP5, the layer structure of rule is presented in JP5G xerogel,
But as addition Hg2+Its layer structure is destroyed afterwards.Thus illustrate Hg2+It being capable of fluorescent quenching identification Hg2+, it is by broken
Bad gel molecular（JP5G）Between hydrogen bond achieve the effect that identification.
Description of the drawings
Fig. 1 is fluorescence intensities of the JP5 in solution and gel.（It is strong that JP5gel represents fluorescence of the JP5 under gel state
Degree, JP5sol represent fluorescence intensities of the JP5 under solution state）.
Fig. 2 is JP5G to Hg2+Fluorescence titration（λex = 345nm）.
Fig. 3 JP5G are to Hg2+Fluorescence matched curve.
The interference--free experiments of Fig. 4 JP5G.
Fig. 5 is JP5 in CDCl3In concentration nuclear-magnetism.
Fig. 6 JP5 powder（Label is powder in figure）, JP5G xerogel（Label is gel in figure）, JP5G
Add Hg2+The infrared spectrum of xerogel（Label is gel+Hg in figure2+）.
Fig. 7 is JP5 powder（a）, JP5G xerogel（b）, JP5G（c）Add Hg2+The scanning electron microscope of xerogel.
Specific implementation mode
Below by specific embodiment to the synthesis of inventive gel factor JP5, the preparation of organogel JP5G and fluorescence
Identify Hg2+Application be described further.
The synthesis of embodiment 1, gelator JP5
（1）The synthesis of compound A：By 12.4 g p methoxy phenols（100 mmol）, 13.8 g potassium carbonate（100 mmol）,
3.3 g potassium iodide（20mmol）, 12.2 g ethyl chloroacetates（100mmol）It is placed in the round-bottomed flask of 500mL, is added 400
The acetone of mL is flowed back for 24 hours at a temperature of 60 DEG C, suitable silica gel is added after reaction stops and is spin-dried for solvent as solvent,
Use column chromatography（Petroleum ether：Ethyl acetate=50:1）Isolated flaxen liquid（(20.16g, 96%).1HNMR
(600MHz, CDCl3), δ 6.82 (q, J=9 Hz, 4H, ArH), 4.53 (s, 2H, OCH2CO), 4.22 (q, J
=7.2 Hz, 2H, OCH2), 3.73 (s, 3H, OCH3), 1.26 (t, J=7.2Hz, 3H, CH3)。
（2）The synthesis of compound PA：By 2.76 g Isosorbide-5-Nitraes-dimethoxy benzene (20 mmol), 1.05 g compounds A（5
mmol）, 0.75g paraformaldehydes（25mmol）It is placed in the round-bottomed flask of 150mL, 1, the 2- dichloroethanes conducts of 100mL is added
2.7 mL boron trifluoride ether are added in solvent（25mmol）It as catalyst, is reacted 30 minutes at a temperature of 30 DEG C, water is added to extract 2-
It 3 times, is added after anhydrous sodium sulfate is dried 1-2 hours and filters in organic phase, proper silica gel is added in filtrate and is spin-dried for solvent,
Use column chromatography（Petroleum ether：Dichloromethane=3:1）Isolated white solid (1.03g, 25 %m.p. 209-210 DEG C)1H NNR (600 MHZ, CDCl3), δ6.93-6.58 (m, 10H, ArH), 4.50 (s, 2H, OCH2CO), 3.82-
3.62 (m, 37H, 27OCH3, 10CH2), 2.19(q, J=6.6 Hz, 2H, OCH2), -1.45(t, J=7.0Hz,
3H, CH3)。
（3）The synthesis of compound PQ：By 2.91 g compounds PA (5 mmol), 1.25 g hydrazine hydrates（25mmol）It is placed in
In the round-bottomed flask of 150mL, the absolute ethyl alcohol of 100 mL is added as solvent, two drop glacial acetic acid are as catalyst, 80 DEG C of temperature
Lower reflux 8h waits for that reaction stops postcooling to room temperature and filters, and obtained solid is washed 3 ~ 5 times with absolute ethyl alcohol, then dry in vacuum
It is dried in dry case, obtains white solid (2.78 g, 98%m.p. 213-214 DEG C),1HNNR (600 MHZ, CDCl3),δ
6.89-6.26(m, 10H, ArH), 4.19(s, 2H, OCH2CO), 3.83-3.48(m, 37H, 27OCH3, 10CH2),
1.63(s, 2H, NH2), 1.17(t, J=7.2 Hz, 1H, NH)。
（4）The synthesis of gelator JP5：By 0.48 g（0.6 mmol）Amidated column [5] aromatic hydrocarbons is placed in the circle of 100mL
In the flask of bottom, 10 mL dichloromethane are added and make solvent, are slowly dropped at 0 DEG C and under stiring 0.053g（0.2mmol）Equal benzene
The dichloromethane solution of three formyl chlorides reacts 12 h at room temperature.It is filtered after reaction stops, obtained solid is washed with dichloromethane
It 3 ~ 5 times, is then dried in vacuum drying chamber, obtains white solid 0.36g.JP5：Yield： 70%; (m.p. 53-54℃),1H NNR (600 MHZ, d 6 -DMSO), δ10.81 (s, 3H, -NH), δ10.30 (s, 3H, -NH), δ8.58 (s,
3H, ArH), δ6.94-6.73 (m, 30H, ArH), δ4.56 (s, 6H, -OCH2), δ3.80-3.66 (m,
111H, 81-OCH3, 30-ArCH2)。
The synthetic route of gelator JP5 is as follows：
The preparation of embodiment 2, organogel JP5G
Weigh gelator（JP5）25 μ L hexamethylenes are added in the gel bottle of 1ml in 0.00125g in gel bottle
Alcohol, heating make gelator fully dissolve, and standing is cooled to room temperature, and form stable surpassing with the aggregated-state induced fluorescence of blue
Molecule organogel JP5G.It is 58 ~ 60 DEG C that organogel JP5G, which turns solubility temperature,.
Embodiment 3, organogel JP5G Hg for identification2+
It takes a series of fritter gel JP5G to be placed on spot plate with capillary, different sun is added in the gel on spot plate respectively
The aqueous solution of ion（C=1mol/L, Hg2+, Ca2+, Mg2+, Ni2+, Cr3+, Cd2+, Pb2+, Ag+, Zn2+, Ba2+, La3+, Eu3+, Tb3 +）, so that liquid level was not had gel just, and be placed on the variation for observing its fluorescence color under the fluorescent lamp that wavelength is 365nm.As a result it sends out
It is existing, only Hg2+Addition the blue-fluorescence of JP5G can be made to quench, and remaining cation addition to the fluorescence intensity of JP5G without bright
Aobvious influence.
Claims (6)
1. one kind being based on the supermolecular gel factor of three columns [5] aromatic hydrocarbons, structural formula is as follows：
。
2. a kind of synthetic method of the supermolecular gel factor based on three columns [5] aromatic hydrocarbons as described in claim 1, is with dichloromethane
Alkane makees solvent, and amidated column [5] aromatic hydrocarbons is with pyromellitic trimethylsilyl chloride with 1:3 molar ratio, in 10 ~ 12h of room temperature reaction；It waits reacting
After filter, obtained solid is washed with dichloromethane, vacuum drying to get,
One kind based on a kind of organogel of the supermolecular gel factor based on three columns [5] aromatic hydrocarbons as described in claim 1, be by
The supermolecular gel factor heating for dissolving for being based on three columns [5] aromatic hydrocarbons is cooled to room temperature in cyclohexanol, forms stable tool
There is the supramolecular organogel of the aggregated-state induced fluorescence of blue.
3. a kind of organogel of the supermolecular gel factor based on three columns [5] aromatic hydrocarbons, feature exist as described in claim 1
In：The mass volume ratio of gelator and cyclohexanol is 50 ~ 60mg/mL.
4. a kind of organogel of the supermolecular gel factor based on three columns [5] aromatic hydrocarbons, feature exist as described in claim 1
In：The solubility temperature that turns of organogel is 58 ~ 60 DEG C.
5. a kind of organogel of the supermolecular gel factor based on three columns [5] aromatic hydrocarbons is known for fluorescence as claimed in claim 3
Other Hg2+。
6. a kind of organogel of the supermolecular gel factor based on three columns [5] aromatic hydrocarbons is known for fluorescence as claimed in claim 6
Other Hg2+, it is characterised in that：In a series of organogels, Hg is added2+, Ca2+, Mg2+, Ni2+, Cr3+, Cd2+, Pb2+, Ag+, Zn2 +, Ba2+, La3+, Eu3+, Tb3+Aqueous solution, only Hg2+Addition the blue-fluorescence of organogel can be made to quench, and remaining is cationic
Addition the fluorescence of organogel cannot be made to be quenched.
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| CN109320454A (en) * | 2018-11-29 | 2019-02-12 | 西北师范大学 | The preparation and application of a kind of bi-component supramolecular organogel and its metal gel |
| CN109400900A (en) * | 2018-10-30 | 2019-03-01 | 西北师范大学 | Supermolecular gel based on the assembling of column [5] aromatic hydrocarbons Subjective and Objective and its application in detection and absorption iron ion |
| CN109536160A (en) * | 2018-12-29 | 2019-03-29 | 西北师范大学 | A kind of preparation and application of tripodia pseudorotaxane supermolecular gel and its metal gel based on pyromellitic trimethylsilyl chloride |
| CN109675525A (en) * | 2019-01-11 | 2019-04-26 | 西北师范大学 | A kind of application of preparation and its absorption and separation methylene blue of metal supermolecular organogel |
| CN110724280A (en) * | 2019-10-18 | 2020-01-24 | 西北师范大学 | Preparation and application of supramolecular polymer hydrogel with thermal response and metal gel thereof |
| CN110790940A (en) * | 2019-10-29 | 2020-02-14 | 西北师范大学 | Bipatripodous supramolecular polymer organogel and preparation and application thereof |
| CN112410021A (en) * | 2019-08-23 | 2021-02-26 | 西北民族大学 | Supermolecule gel capable of performing single selective fluorescent recognition on arsenite ions and preparation and application thereof |
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| CN109400900B (en) * | 2018-10-30 | 2021-02-05 | 西北师范大学 | Supermolecule gel assembled based on column [5] arene main-object and application thereof in detection and adsorption of iron ions |
| CN109320454A (en) * | 2018-11-29 | 2019-02-12 | 西北师范大学 | The preparation and application of a kind of bi-component supramolecular organogel and its metal gel |
| CN109320454B (en) * | 2018-11-29 | 2021-07-09 | 西北师范大学 | Bi-component supermolecule organogel and preparation and application of metal gel thereof |
| CN109536160A (en) * | 2018-12-29 | 2019-03-29 | 西北师范大学 | A kind of preparation and application of tripodia pseudorotaxane supermolecular gel and its metal gel based on pyromellitic trimethylsilyl chloride |
| CN109675525A (en) * | 2019-01-11 | 2019-04-26 | 西北师范大学 | A kind of application of preparation and its absorption and separation methylene blue of metal supermolecular organogel |
| CN112410021A (en) * | 2019-08-23 | 2021-02-26 | 西北民族大学 | Supermolecule gel capable of performing single selective fluorescent recognition on arsenite ions and preparation and application thereof |
| CN112410021B (en) * | 2019-08-23 | 2023-08-08 | 西北民族大学 | Supermolecule gel capable of identifying arsenite ions through single selective fluorescence and preparation and application thereof |
| CN110724280A (en) * | 2019-10-18 | 2020-01-24 | 西北师范大学 | Preparation and application of supramolecular polymer hydrogel with thermal response and metal gel thereof |
| CN110724280B (en) * | 2019-10-18 | 2022-05-24 | 西北师范大学 | Preparation and application of supramolecular polymer hydrogel with thermal response and metal gel thereof |
| CN110790940A (en) * | 2019-10-29 | 2020-02-14 | 西北师范大学 | Bipatripodous supramolecular polymer organogel and preparation and application thereof |
| CN110790940B (en) * | 2019-10-29 | 2021-06-11 | 西北师范大学 | Bipatripodous supramolecular polymer organogel and preparation and application thereof |
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